It is a multi-story romantic comedy about the people who work on weddings to create the perfect day for a loving couple - while their own relationships are outlandish, odd, crazy and far from perfect.

The story of Courtney Bennett, a former Olympic skating hopeful who teaches skating classes and runs the city's outdoor public skating oval in the Common behind City Hall. When Mayor Greenwood announces the imminent closing of the skating oval, Courtney faces off with former NHL hockey player Noah Tremblay, a single dad who runs the new indoor skating center, to try to save the public rink and the Christmas Carnival she hosts on the Common each Holiday season. Courtney and Noah bond over his daughter Grace who joins Courtney's skating class and Courtney discovers a secret connection between Noah and the Mayor that could be the Mayor's soft spot. Together Courtney and Noah devise a plan to keep the skating oval open and fall in love along the way.

Merry Griffin is a relationship expert whose blog, which espouses her checklist of dating rules, has a substantial following. She is parlaying that blog into her first book outlining how those rules have led to her finding her Mr. Right, fiancé Dale Westfield. In this approach to Christmas, the book is being edited by her best friend, Darlene Walters, for Littlefield, the boutique Boston publishing house where she works as a junior editor, it ready to hit the store shelves in time for next Christmas. The problem is is that Dale is not actually her Mr. Right, but someone she encountered briefly in a coffee shop as he was waiting for a blind date, he solely the inspiration for Merry's fantasy love life, something that Darlene knows, but which they learn Darlene's boss, publisher Sonia Hendricks, would have issue with in the reality being what makes Merry's manuscript stand out from the pack. As Darlene and Merry head to Darlene's hometown of Snowbridge, VT for the Christmas holidays to strategize about how they will deal with this problem which was unintentional in Merry just wanting to help people with the book, Sonia beats them to the punch when she tracks them down in Snowbridge in discovering that Dale is not real. As this book could make or break the company which also means Darlene's job, Sonia provides an ultimatum for Merry to come up with another solid book idea before she leaves town just prior to the 25th. What happens with the book and thus Merry's writing career is affected by whether she is able to demonstrate that her rules do lead to a love life, especially as they apply to herself. There are seemingly two potential men that could fill the void as that Mr. Right for Merry, each who has an issue in filling that void. The first is New York restaurateur James Smith, who happens to be Darlene's ex-boyfriend for who Darlene does not want to admit she still has feelings, despite his actions toward Merry. And the second is Darlene's brother, Adam Walters who unexpectedly came back to Snowbridge having long worked overseas doing charity aide work, the latest post in the jungles of Guatemala, while he figured out what he wanted to do with his life. His surprise visit is in part to make a geographic split with his now ex-girlfriend Julie and in part to make that declaration of his professional future: wanting to take over the family business, Walters Gift Shop and Tree Lot, he who would be the fourth generation of Walters to run it. That declaration surprises his and Darlene's parents, as he had never made any indication of wanting to do so before now. The primary issues with Adam and Merry are that they had a mutual attraction in their one and only encounter ten years ago which led to nothing for various reasons, but more importantly that Adam does not believe in any of the checklist items about which Merry writes.

Julia returns to her hometown for Christmas to drown her sorrows after her recent political campaign for city council ended in a landslide loss.

It's the Christmas season, which marketing executive Lauren Kim usually spends happily with her divorced father Leo and her stepmother Yung, her mother largely out of the picture after she abandoned the family just before Christmas years ago to travel the world unencumbered as was her want. Who has a standing invitation to spend Christmas with them is Lauren's BFF Nate Sagar, a social worker who went into the profession to pay it forward in having been brought up in the foster care system. Nate accepts the invitation whenever he and Lauren are not in respective relationships, this year being the case in neither having been in such for over a year. Nate has temporarily taken himself off the dating market in focusing on setting up a community center, which he has completed just in time for the foster kids to celebrate Christmas there this year. Late one night as Lauren dozes off working on a last minute work project due in one week on Christmas Eve, she is visited by who she finally comes to understand is the spirit of her first ever boyfriend, a forever fifteen year old Tyler Mirsky, who informs her that she in turn will be visited over the next week by the spirits of three other past boyfriends hoping to show her the errors in her pattern of behavior. While those three boyfriends - Jake, Henry and Logan - are able to show Lauren some of those errors, most specifically her seeming fear of commitment, and the constant of Nate always in the picture, she may not fully realize all the patterns and the consequences of her behavior until she sees the result of both in her and Nate's future.